ArticleNature chemistry2017
Synthesis facilitates an understanding of the structural basis for translation inhibition by the lissoclimides.
Article in Nature chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 46 citations in OpenAlex.
- Aspartimide Modification in RiPP Natural Products.Biochemistry · 2026Review
- Context-dependent translation inhibition as a cancer therapeutic modality.Nature communications · 2026Article
- Synthesis of Differentially Halogenated Lissoclimide Analogues To Probe Ribosome E-Site Binding.ACS chemical biology · 2025Article
- Unifying principles for the design and evaluation of natural product-inspired compound collections.Chemical science · 2025Review
- Computational Approaches to Enzyme Inhibition by Marine Natural Products in the Search for New Drugs.Marine drugs · 2023Review
- Harnessing Natural Products by a Pharmacophore-Oriented Semisynthesis Approach for the Discovery of Potential Anti-SARS-CoV-2 Agents.Angewandte Chemie (International ed. in English) · 2022Article
- Inhibition of the Eukaryotic 80S Ribosome as a Potential Anticancer Therapy: A Structural Perspective.Cancers · 2021Review
- The Recurring Roles of Chlorine in Synthetic and Biological Studies of the Lissoclimides.Accounts of chemical research · 2021Review
- Expanding the antibacterial selectivity of polyether ionophore antibiotics through diversity-focused semisynthesis.Nature chemistry · 2021Article
- Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones.Journal of medicinal chemistry · 2020Article
- Bridging the gap between natural product synthesis and drug discovery.Natural product reports · 2020Review
- A Quick Guide to Small-Molecule Inhibitors of Eukaryotic Protein Synthesis.Biochemistry. Biokhimiia · 2020Review
- A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K.Journal of the American Chemical Society · 2019Article
- Understanding the role of intermolecular interactions between lissoclimides and the eukaryotic ribosome.Nucleic acids research · 2019Article
- Ascidian Toxins with Potential for Drug Development.Marine drugs · 2018Review
Corrections and comments
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Authors and funding
15 authors at 4 institutions in 3 countries.
Funding
Abstract
The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semisynthesis and analogue-oriented synthesis approaches provide a series of lissoclimide natural products and analogues that expand the structure-activity relationships (SARs) in this family. The semisynthesis approach yielded significant quantities of chlorolissoclimide (CL) to permit an evaluation against the National Cancer Institute's 60-cell line panel and allowed us to obtain an X-ray co-crystal structure of the synthetic secondary metabolite with the eukaryotic 80S ribosome. Although it shares a binding site with other imide-based natural product translation inhibitors, CL engages in a particularly interesting and novel face-on halogen-π interaction between the ligand's alkyl chloride and a guanine residue. Our analogue-oriented synthesis provides many more lissoclimide compounds, which were tested against aggressive human cancer cell lines and for protein synthesis inhibitory activity. Finally, computational modelling was used to explain the SARs of certain key compounds and set the stage for the structure-guided design of better translation inhibitors.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.